Is curcumin an active suicidal antioxidant only in the aqueous environments?
Abstract Curcumin is a natural polyphenol with various bioactivities, including anti-tumor, antioxidant, and anti-inflammatory. Despite curcumin’s therapeutic benefits, limited water solubility and rapid hydrolytic degradation are important challenges in using of curcumin for clinical applications. Therefore, this report aimed to examine the stability and antioxidant activity of curcumin in different environments and to find out the mechanism of action through which curcumin shows its radical scavenging activity. Results of this study not only indicated that degradation of curcumin is water-dependent but also suggested its degradation mechanism is distinct from general acid/base catalysis and nucleophilic attack of water hydroxyl ion ($ OH^{−} $) had apparently negligible role in rapid hydrolytic degradation of curcumin. We confirmed that curcumin is solely responsible for its antioxidant activity in aqueous media and its degradation is a spontaneous autoxidation. More importantly, curcumin exhibited rapid decomposition in the presence of excessive $ O_{2} $ or free radicals induced by oxidizing agents (TBHP and $ H_{2} %$ O_{2} $) due to its protective potential against oxidative stress. The possible attack site of free radicals in curcumin is in the first step of curcumin degradation, where phenoxyl radical is produced. On the other hand, curcumin degradation and scavenging activity reduced when it entered into the hydrophobic cavity of BSA or casein molecule. Surprisingly, in soybean oil, curcumin showed the weak antioxidant activity compared to TBHQ (as a potent synthetic antioxidant for frying oils), implying that curcumin did not have significant antioxidant potential in oily/hydrophobic environments. Overall, our findings confirmed that curcumin in aqueous buffer is quickly degrades while at the same time scavenging of free radicals. The presented results are novel and might be interesting as the analysis of physicochemistry of curcumin has been gaining importance in view of biological significance..
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2022 |
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| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:19 |
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| Enthalten in: |
Journal of the Iranian Chemical Society - 19(2022), 8 vom: 03. März, Seite 3441-3450 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Mehrabi, Masomeh [VerfasserIn] |
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| Links: |
Volltext [lizenzpflichtig] |
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| Themen: |
Antioxidant activity |
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| Anmerkungen: |
© Iranian Chemical Society 2022 |
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| doi: |
10.1007/s13738-022-02538-3 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a Abstract Curcumin is a natural polyphenol with various bioactivities, including anti-tumor, antioxidant, and anti-inflammatory. Despite curcumin’s therapeutic benefits, limited water solubility and rapid hydrolytic degradation are important challenges in using of curcumin for clinical applications. Therefore, this report aimed to examine the stability and antioxidant activity of curcumin in different environments and to find out the mechanism of action through which curcumin shows its radical scavenging activity. Results of this study not only indicated that degradation of curcumin is water-dependent but also suggested its degradation mechanism is distinct from general acid/base catalysis and nucleophilic attack of water hydroxyl ion ($ OH^{−} $) had apparently negligible role in rapid hydrolytic degradation of curcumin. We confirmed that curcumin is solely responsible for its antioxidant activity in aqueous media and its degradation is a spontaneous autoxidation. More importantly, curcumin exhibited rapid decomposition in the presence of excessive $ O_{2} $ or free radicals induced by oxidizing agents (TBHP and $ H_{2} %$ O_{2} $) due to its protective potential against oxidative stress. The possible attack site of free radicals in curcumin is in the first step of curcumin degradation, where phenoxyl radical is produced. On the other hand, curcumin degradation and scavenging activity reduced when it entered into the hydrophobic cavity of BSA or casein molecule. Surprisingly, in soybean oil, curcumin showed the weak antioxidant activity compared to TBHQ (as a potent synthetic antioxidant for frying oils), implying that curcumin did not have significant antioxidant potential in oily/hydrophobic environments. Overall, our findings confirmed that curcumin in aqueous buffer is quickly degrades while at the same time scavenging of free radicals. The presented results are novel and might be interesting as the analysis of physicochemistry of curcumin has been gaining importance in view of biological significance. | ||
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